EP0097232A2 - Procédé de préparation de 4-(trialkylammonium)-acéto-acétarylides - Google Patents
Procédé de préparation de 4-(trialkylammonium)-acéto-acétarylides Download PDFInfo
- Publication number
- EP0097232A2 EP0097232A2 EP83104127A EP83104127A EP0097232A2 EP 0097232 A2 EP0097232 A2 EP 0097232A2 EP 83104127 A EP83104127 A EP 83104127A EP 83104127 A EP83104127 A EP 83104127A EP 0097232 A2 EP0097232 A2 EP 0097232A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- solvents
- preparation
- trialkylammonium
- mmol
- ethyl acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000005270 trialkylamine group Chemical group 0.000 claims abstract description 8
- 125000005208 trialkylammonium group Chemical group 0.000 claims abstract description 5
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 2
- YTYSUPNFVFLVND-UHFFFAOYSA-N CC(CC(NC1=CC=CC=C1)=O)=O.Cl Chemical compound CC(CC(NC1=CC=CC=C1)=O)=O.Cl YTYSUPNFVFLVND-UHFFFAOYSA-N 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- -1 -OC 2 H 5 Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CJLSDBRIXZFCKV-UHFFFAOYSA-N 4-chloro-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)CC(=O)NC1=CC=CC=C1 CJLSDBRIXZFCKV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical group CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RJTROOIXLNVHNB-UHFFFAOYSA-N 4-bromo-3-oxo-n-phenylbutanamide Chemical compound BrCC(=O)CC(=O)NC1=CC=CC=C1 RJTROOIXLNVHNB-UHFFFAOYSA-N 0.000 description 1
- OINZDKQLTANSIR-UHFFFAOYSA-N 4-chloro-n-(4-nitrophenyl)-3-oxobutanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)CC(=O)CCl)C=C1 OINZDKQLTANSIR-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229950010007 dimantine Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
- KCXJQNDNGLRYBN-UHFFFAOYSA-N n-(4-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 KCXJQNDNGLRYBN-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
Definitions
- the term "lower alkyl” means alkyl groups with 1-6, preferably 1-4 carbon atoms.
- Pigments accumulate more or less intensively in the course of the manufacturing process to form larger agglomerates.
- these assemblies must be broken down - dispersed - into their individual components as far as possible. The extent to which this succeeds influences almost all properties, durability and fastness.
- additives are added to the pigments already during manufacture.
- hyper-dispersants can be polyhydroxystearic acid compounds, for example, for non-polar systems.
- Polymers and copolymers, longer-chain polyurine are used for polar systems
- Substance compounds, polyacid esters or quaternary ammonium sulfates used Progress in Org.Coatings, 5 (1977), 237-343).
- the aim of the present invention is to eliminate the disadvantages of the known systems.
- Advantageous trialkylamine compounds are those in which R 1 and R 2 are identical or different and are lower alkyl radicals having 1 to 4 carbon atoms and R 3 is a higher alkyl radical having 6 to 18 carbon atoms.
- trialkylamine residues are e.g. Dimethyl-hexyl, dimethyldodecyl, dimethyl-octadecylamine residues etc.
- acetoacetic acid arylide residues those are used which are known as coupling components in the usual pigments. These are: acetoacetic anilide, -o-chloroanilide, -o-anisidide, -o-toluidid, -m-xylidid, -p-anisidide, -p-toluidid, -p-phenetidid, -2-methyl-4-chloroanilide, 2,4-dimeth-oxyanilide, -2,5-dimethoxyanilide, -2-methoxy-5-chloroanilide, -2,5-dimethoxy-4-chloroanilide, -p-nitroanilide, -3-chloroanilide, -2-ethyl 6-methylanilide, -2,6-dimethylanilide, etc.
- novel compounds according to the invention are prepared by reacting the corresponding 4-haloacetoacetic arylides with the corresponding trialkylamine, at temperatures from -10 to + 50 ° C. and in the presence of organic solvents. Temperatures of 0 to 30 ° C. are preferably used. It is advantageous to use the trialkylamines in excess; expediently, 1.1 to 1.6 moles of trialkylarine are used per mole of arylide.
- Solvents although OH-group-containing organic solvents such as methanol and ethanol can also be used, are advantageously OH-group-free solvents. Working in OH-group-free solvents makes the isolation of the end products easier and the yields are higher.
- solvents are aromatic hydrocarbons, e.g. Benzene, toluene, chlorinated hydrocarbons, e.g. Carbon tetrachloride, di-, tri- and tetrachloroethane, chlorobenzene, dichlorotoluene, chloroform, dichloromethane.
- polar aprotic solvents such as ethyl acetate, acetonitrile, acetone, dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric acid triamide etc. are used as solvents.
- the 4-chloroacetessigarylides used are preferably the 4-chloro or 4-bromo derivatives.
- the 4- (trialkylammonium) acetoacetgrylidenes according to the invention can be reacted, for example, with suitable diazonium compounds in a manner known per se and azo dyes can thus be prepared.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT83104127T ATE22881T1 (de) | 1982-06-18 | 1983-04-27 | Verfahren zur herstellung von 4(trialkylammonium)-acetoacetaryliden. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3769/82 | 1982-06-18 | ||
| CH3769/82A CH649282A5 (de) | 1982-06-18 | 1982-06-18 | Verfahren zur herstellung von 4-(trialkylammonium)-acetoacetaryliden. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0097232A2 true EP0097232A2 (fr) | 1984-01-04 |
| EP0097232A3 EP0097232A3 (en) | 1984-12-19 |
| EP0097232B1 EP0097232B1 (fr) | 1986-10-15 |
Family
ID=4263089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83104127A Expired EP0097232B1 (fr) | 1982-06-18 | 1983-04-27 | Procédé de préparation de 4-(trialkylammonium)-acéto-acétarylides |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4558158A (fr) |
| EP (1) | EP0097232B1 (fr) |
| JP (1) | JPS597145A (fr) |
| AT (1) | ATE22881T1 (fr) |
| CH (1) | CH649282A5 (fr) |
| DE (1) | DE3366915D1 (fr) |
| DK (1) | DK267683A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3636551A1 (de) * | 1986-10-28 | 1988-05-05 | Dow Chemical Co | Fungizide 4-monohalogenacetoacetanilide |
| US6099635A (en) * | 1999-04-09 | 2000-08-08 | Lonza Ag | Acetoacetylated suspensions in pigment applications |
| US20050236299A1 (en) * | 2004-04-27 | 2005-10-27 | Mark Weber | Folded material containment packages and related methods of packaging folded material products |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014046A (en) * | 1960-10-21 | 1961-12-19 | Monsanto Chemicals | Quaternary ammonium iodides |
| CH543504A (de) * | 1971-03-25 | 1973-10-31 | Lonza Ag | Verfahren zur Herstellung 1-substituierter 4-Aminopyrrolin-3-one-(2) |
| US4015013A (en) * | 1972-10-16 | 1977-03-29 | Rhone-Poulenc S.A. | Certain quaternary ammonium salts used to control gram-negative bacteria |
| DE2915250A1 (de) * | 1979-04-14 | 1980-10-30 | Basf Ag | Salze von alpha -aminoacetaniliden |
| GB2112797B (en) * | 1981-10-05 | 1985-06-19 | Koege Kemisk Vaerk | Azopigments |
-
1982
- 1982-06-18 CH CH3769/82A patent/CH649282A5/de not_active IP Right Cessation
-
1983
- 1983-04-27 AT AT83104127T patent/ATE22881T1/de not_active IP Right Cessation
- 1983-04-27 DE DE8383104127T patent/DE3366915D1/de not_active Expired
- 1983-04-27 EP EP83104127A patent/EP0097232B1/fr not_active Expired
- 1983-06-07 US US06/501,898 patent/US4558158A/en not_active Expired - Fee Related
- 1983-06-10 DK DK267683A patent/DK267683A/da not_active Application Discontinuation
- 1983-06-14 JP JP58107599A patent/JPS597145A/ja active Pending
-
1984
- 1984-09-20 US US06/652,484 patent/US4552983A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE22881T1 (de) | 1986-11-15 |
| DK267683D0 (da) | 1983-06-10 |
| US4552983A (en) | 1985-11-12 |
| DK267683A (da) | 1983-12-19 |
| CH649282A5 (de) | 1985-05-15 |
| EP0097232B1 (fr) | 1986-10-15 |
| DE3366915D1 (en) | 1986-11-20 |
| US4558158A (en) | 1985-12-10 |
| EP0097232A3 (en) | 1984-12-19 |
| JPS597145A (ja) | 1984-01-14 |
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